Poll: Would You Date Your Friend's Ex-Boyfriend? By YourTango EmailPrint Comment? Share on Facebook He's really hot. You're really compatible. What do you do? You've fallen in love and he likes you too. Unfortunately, he is also your friend's ex-boyfriend. So which would you choose: love or friendship? Poll: Would You Date Your Friend's Ex-Boyfriend?: Never. That goes against the basic rules of friendship. Maybe. It depends on how long they were dating and who broke it off. Why not? All's fair in love and war. Yes, as long as she was OK with it. If she wasn't I wouldn't bother dating him.